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A decade before mounting his blusterous campaign for president of the United States, Donald Trump set his sights on a far more audacious title: King of Seattle Real Estate. Yep, just before the Great Recession, the billionaire and sentient comb-over wanted to build an 82-story hotel and condo in the central business district. And he almost succeeded. 

If the thought of Trump erecting one of his conspicuously lavish hotels in the home of inconspicuous wealth makes you click your tongue and clutch your North Face fleece a little tighter, you can direct your ire at commercial real estate developer Spencer Alpert. In the early 2000s his dealings with Trump were limited to a proposed mixed-use project across the street from the then-new home of the NBA’s Dallas Mavericks that fell through when Alpert found a higher bidder. (Who just happened to be Ross Perot Jr.) Rather than sour their relationship, Alpert’s 11th-hour change of heart was the beginning of a friendship that soon included Trump’s children, Don Jr. and Ivanka. 

It wasn’t until 2006, though, that the two camps discussed working together again. By that time, Alpert had begun exploring projects outside of the Dallas–Fort Worth area and suggested Seattle as the site of a new Trump hotel. The siblings agreed, and within the year Ivanka and Alpert were scouting properties in the city and, at his urging, Bellevue. One trip across the bridge was enough. “When we were driving back she said, ‘You know, Spence, I’m glad you took me over there, but the Trumps aren’t interested in being in a secondary market,’” Alpert recalls with a laugh. “Bellevue was below their standards.”

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The sky was the limit for Trump’s Seattle hotel, which would have dwarfed Columbia Tower. Early plans called for a structure at least a quarter-mile tall.

It may have been below their standards, but it might have been cheaper. Remember, this was at the height of the real estate bubble, and property owners could name their price when buyers came calling. And if that buyer’s name was Trump, the markup was likely to be severe—and not just because of his supposedly deep pockets. Matt Griffin of Pine Street Group, which developed Pacific Place, says Trump’s personality may have caused owners to think, “I don’t want him in town. I’m going to [quote a price that will] make him puke.”

With that in mind, Ivanka ordered Alpert to keep the Trump name out of any negotiations in the early stages. “It was really double-oh-seven stuff,” says a real estate agent who helped in the property hunt. By early 2007, Alpert had what he calls a “firm deal” to buy the office building behind Bed Bath and Beyond at Third Avenue and Stewart, from Clise Properties, which owned a large swath of land extending north to South Lake Union. The price: a reasonable $550 per square foot. At about that time, the Puget Sound Business Journal got a tip that the Trumps were in town and published a gossipy story on the development. Alpert went into spin mode, offering an official interview with Ivanka to The Seattle Times, and on March 8, there were Donald and Ivanka on the front page, above the fold: “A Trump Tower in Seattle? It Could Happen,” read the headline.

It’s hard to say if that leak is responsible for what happened next, but the project began to unravel quickly. That spring Alpert’s contact at Clise, Richard Stevenson, stopped answering his calls. (Alpert says the two ran into each other years later, and Stevenson admitted the owners had decided that if Donald Trump was willing to pay $550 a square foot for just that piece of property, maybe Clise could interest a well-heeled buyer in their entire downtown parcel. Stevenson didn’t respond to multiple requests for comment.)

Alpert got close again later that year, this time on a piece of property near Columbia Center, and he even went so far as to commission designs from local commercial architecture firm Callison. The renderings are striking—if not slightly bland—in part because the gleaming, silvery building, which resembles a scalpel, would have dwarfed the nearby Columbia Tower and become the tallest structure in Seattle. And in true Trump style, the $700 million project would have been over the top: The main tower was to include a three-story private club managed by the same firm that operates the Columbia Tower Club. A second tower, scheduled to come online a few years later, was designed with retail, 50 floors of condos, and a sky bridge that would connect to the first structure. “It was the best site in Seattle,” Alpert says now.

With the move south, however, the land price had nearly doubled, and soon talks broke off. That was more than seven years ago, though, and the commercial real estate market has rebounded and then some. And just like Donald’s presidential aspirations, Alpert’s dream of a Trump Tower in Seattle won’t go away quietly. Because despite our low-key style—“You see Gates and Ballmer running around in clothes with holes in them,” says Pine Street Group’s Griffin—Alpert thinks it would be an opportunity too big to pass up.

In other words, don’t be surprised if in a couple years we’re forced to say, “Welcome home, President Trump.”

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